Real Estate Investment Properties for Sale in Winnetka, IL
Looking for investment property in Winnetka, IL with high ROI ?
Explore a variety of short-term homes & houses in Winnetka, IL. Invest wisely with VRBO & Winnetka, IL Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.
Investment Property for Sale in Winnetka, IL
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
305 Poplar StreetWINNETKA, ILOne of East Winnetka's most coveted locations! Handsome brick Colonial with separate studi... |
3 beds | 3 baths | 3,128 sq.ft. |
$1,250,000 |
Airbnb cash on cash: -1.14%
|
275 White Oak LaneWINNETKA, ILFirst Time on the Market - Coveted White Oak Lane Tucked away on a private 1/2 acre lot... |
4 beds | 6 baths | 3,598 sq.ft. |
$1,599,000 |
Airbnb cash on cash: -0.61%
|
342 Rosewood AvenueWINNETKA, ILSophisticated perfection on an extra wide lot in one of Winnetka's most picturesque neighb... |
4 beds | 5 baths | 4,585 sq.ft. |
$1,995,000 |
Airbnb cash on cash: -0.45%
|
650 Winnetka Mews #310WINNETKA, ILFabulous opportunity to own this 2 Bed/2 Bath condo in sought after Winnetka Mews building... |
2 beds | 2 baths | 1,630 sq.ft. |
$489,000 |
Airbnb cash on cash: -2.88%
|
334 Woodland AvenueWINNETKA, ILAbsolutely breathtaking "better-than-new" East Winnetka Classic on an oversized (75' wide)... |
4 beds | 5 baths | 3,748 sq.ft. |
$2,799,000 |
Airbnb cash on cash: -0.95%
|
1333 Tower RoadWINNETKA, ILBeautifully reimagined in 2023, this custom Hemphill-designed home blends modern elegance ... |
5 beds | 6 baths | 3,921 sq.ft. |
$2,100,000 |
Airbnb cash on cash: N/A
|
Real Estate investment in Winnetka, IL
There are 9 properties for sale in the city of Winnetka . The median list price in Winnetka is $1,995,000 and the average price per square foot is $548. In December 2025, the average monthly cash on cash return in Winnetka is N/A%. The average monthly rental income in Winnetka is $4,113.